Every WWE Money In The Bank Winner Ranked Worst to Best
From Seth Rollins to Jack Swagger, not all Money in the Bank winners are created equal.
Money in the Bank is one of the most regularly-anticipated events in WWE’s calendar year. Regardless of the actual quality of the MiTB ladder matches (which vary), everyone always looks forward to who will hold that briefcase. Whether they be young upstarts getting primed for their major push, or listless veterans in need of a new direction and purpose, the MiTB briefcase has been an effective way to jumpstart careers and shake up the main event scene.
However, despite the success stories Money in the Bank has brought, some have been rather disappointing, and at their worst, completely pointless. Sometimes, the winner just isn’t ready for a world title run. Sometimes, they’re booked poorly after cashing in and winning the gold. Sometimes, they don’t even get to cash in.
Still, with the mixture of failure and success, it’s always a question of who the best and worst MiTB winners are. This lists looks at every winner of a Money in the Bank briefcase and ranks them from worst use of the concept to best use. Who got the most out of holding the briefcase, and who got the least?
17. Mr. Kennedy (2007)
It’s only appropriate to have someone who didn’t even get to attempt a cash-in.
In the mid-2000s, WWE were primed to push one Ken Anderson, known then as Ken Kennedy, or Mr. Kennedy, or MISTEERRRRRRRR KENNNNNEEDDYYYYYYYY (whichever you prefer). With a solid heel gimmick and a high-profile feud with The Undertaker under his belt, 2007 looked to be Kennedy’s year as he won the Money in the Bank match at WrestleMania 23. Supposedly, the plan was for Kennedy to become WWE champion, and then be revealed as Vince McMahon’s illegitimate son, which would lead to a feud with Triple H that would culminate at the following ‘Mania.
Unfortunately, we saw none of that. Kennedy suffered a legitimate injury and ended up losing his briefcase to Edge on an episode of SmackDown. From there, injuries, brand switches, a wellness policy violation, and massive heat with company golden boy Randy Orton would keep Kennedy mired in midcard limbo until his release in May of 2009.
It’s unclear how successful Kennedy would have been had the plans for him come to fruition. However, this is not a list of “what ifs,” and what Kennedy is is the answer to the trivia question “Who is the only Money in the Bank winner to lose their briefcase without cashing in?”